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Chemical Structure| 926663-00-5 Chemical Structure| 926663-00-5

Structure of 926663-00-5

Chemical Structure| 926663-00-5

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Product Details of [ 926663-00-5 ]

CAS No. :926663-00-5
Formula : C9H9N3O3
M.W : 207.19
SMILES Code : O=C(C1=C2NC(C=CN2N=C1)=O)OCC
MDL No. :MFCD12407818
InChI Key :PCKVUOAPCLMZJI-UHFFFAOYSA-N
Pubchem ID :135513254

Safety of [ 926663-00-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 926663-00-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 9
Fraction Csp3 0.22
Num. rotatable bonds 3
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 51.9
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

76.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.81
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.06
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.2
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.4
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.72
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.61

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.33
Solubility 9.63 mg/ml ; 0.0465 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.09
Solubility 16.7 mg/ml ; 0.0804 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.11
Solubility 1.62 mg/ml ; 0.0078 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.61 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.14

Application In Synthesis of [ 926663-00-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 926663-00-5 ]

[ 926663-00-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1001-26-9 ]
  • [ 6994-25-8 ]
  • [ 926663-00-5 ]
YieldReaction ConditionsOperation in experiment
17.1 g With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; A) ethyl 5-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate To a solution of ethyl 3-amino-1H-pyrazole-4-carboxylate (15.0 g) and <strong>[1001-26-9]ethyl 3-ethoxy-2-propenoate</strong> (21.0 mL) in N,N-dimethylformamide (322 mL) was added cesium carbonate (56.7 g). The reaction mixture was stirred overnight at 100° C., water was added, and acetic acid was sequentially added to adjust the pH to about 4. The obtained solid was collected by filtration, and washed with water to give the title compound (17.1 g). 1H NMR (300 MHz, DMSO-d6) delta 1.28 (3H, t, J=7.0 Hz), 4.27 (2H, q, J=6.9 Hz), 6.14 (1H, d, J=7.9 Hz), 8.13 (1H, s), 8.56 (1H, d, J=7.9 Hz), 11.75 (1H, brs).
17.1 g With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; The 3-amino -1H-pyrazole-4-carboxylic acid ethyl ester (15.0g) and <strong>[1001-26-9]3-ethoxy-2-acrylic acid ethyl ester</strong> (21.0 ml) for N, N- dimethyl formamide (322 ml) is added in the solution cesium carbonate (56.7g). The reaction mixtures in 100 °C stirring overnight, add water, and adding acetic acid in order to adjust the pH to about 4. The collection of the solid by filtering, and by water cleaning and generates a title compound (17.1g).
  • 2
  • [ 1001-26-9 ]
  • [ 1260243-04-6 ]
  • [ 926663-00-5 ]
YieldReaction ConditionsOperation in experiment
91% With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2h; To a mixture of ethyl 3-amino-1H-pyrazole-4-carboxylate (29) (30.0 g, 193 mmol) and <strong>[1001-26-9]ethyl 3-ethoxy-2-propenoate</strong> (cis- and trans-mixture, 41.9 mL, 290 mmol) in DMF(387 mL) was added cesium carbonate (113 g, 348 mmol). Themixture was stirred at 100°C for 2 h, diluted with water andthen acidified to pH ca. 5 with AcOH. The resulting solid wasfiltered by filtration, washed with water and dried to afford 30(36.4 g, 176 mmol, 91percent) as a beige solid. 1H-NMR (300 MHz,DMSO-d6) delta: 1.28 (3H, t, J=7.1 Hz), 4.28 (2H, q, J=7.1 Hz),6.15 (1H, d, J=7.9 Hz), 8.13 (1H, s), 8.57 (1H, d, J=7.9 Hz),11.73 (1H, br s).
 

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Technical Information

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